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<h1><a href="https://archiveofourown.org/works/23863567">Payment In Kind</a> by <a class='authorlink' href='https://archiveofourown.org/users/EnsignOrSutin/pseuds/EnsignOrSutin'>EnsignOrSutin</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Compilation of Final Fantasy VII, Final Fantasy VII Remake - Fandom</td></tr>

<tr><td><b>Genre:</b></td><td>F/M, Learning curve, Male Virginity, Sexual Inexperience, quick study, unexpected visit</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-04-26</td></tr>

<tr><td><b>Updated:</b></td><td>2020-04-29</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-02 22:42:47</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>2</td></tr>

<tr><td><b>Words:</b></td><td>8,762</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/23863567</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/EnsignOrSutin/pseuds/EnsignOrSutin</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Jessie can't wait until tomorrow night afterall...</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Jessie Rasberry/Cloud Strife</td></tr>

<tr><td><b>Comments:</b></td><td>13</td></tr>

<tr><td><b>Kudos:</b></td><td>88</td></tr>

</table>

<a name="section0001"><h2>1. Chapter 1</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Takes place after Cloud, Jessie, Biggs, and Wedge have parachuted back to the Sector 7 Slums.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>“So I know I said I'd pay you in full tomorrow night, buuuuut....”</p><p>Cloud had barely taken his boots off by the time Jessie had knocked on his door, “But you just couldn't wait?” he asked, his expression betraying the fact that it wasn't even a question. He had to admit he was surprised that she'd made it here so quick without catching up to him, but not really that surprised that she had turned up at all. Especially after the way her sarcastic innocence had drawn out her open ended conjunction.</p><p>“I hope that's not a bad thing?” Jessie replied, and made a motion to be let in. Conscious of that fact that Marle, or indeed anyone, could easily see his guest knocking on his door if they were awake at such an hour, Cloud quickly stepped back and let her enter the single room which was as sparsely decorated as his usual outgoing persona. “Ok, so I'm gonna be straight with you” she added as soon as Cloud had closed the door.</p><p>“Have to admit though, I thought that was all just an act” retorted Cloud as he interrupted what she was about to say next. Despite being able to stare down any enemy in battle her sudden appearance had made him nervous, which in turn was making him more articulate than normal. <em>Well I certainly got his attention at least</em>, Jessie mused.</p><p>“Well if I'm gonna be straight” she continued as Cloud began to shift somewhat uncomfortably, “I guess I might as well be completely straight. Yeah, it is an act.” She had the full attention of her intimate audience of one as he pondered what else couldn't wait until tomorrow if her flirting hadn't been serious. “...But also it isn't”, she finished with a shrug. With Jessie stood in front of him in the privacy of his room, her proposition now more enigmatic yet somehow also more honest, not for the first time Cloud looked at her armour as he studied her, and the fact it took the role of being a breastplate a little too literally.</p><p>He wondered what she was trying to say by wearing it and whether the ample curves in the thick metal plating were nothing more than a facade, an extension of her flirty personality used to hide the real her underneath? Or were they really there to accommodate her own voluptuous build? He also began to wonder if they were there to act as a distraction before the realisation that if they were, then they were certainly working. He brought his eyes back to Jessie's face with a start.</p><p>“That's why I love acting so much” she added. Having gladly allowed Cloud all the time he wanted to look her over, her response was once more filled with enthusiasm and confidence as though it was meant to be all the explanation Cloud needed.</p><p>“So you can hide behind being someone else?” Cloud asked. Though he posed the question out of curiosity as to what was happening in Jessie's mind, his loins were already beginning to stir thanks to his continued thoughts about the body she was hiding under her armour.</p><p>“So I can hide myself in plain sight” she replied simply. “When I flirt with people, I go over the top so they see it as an act.”</p><p>“I guess that makes sense?” Cloud confirmed, his questioning not so much at what she said but at how to take it in.</p><p>“With something like acting, you can truly show the world those parts of you that you can't express elsewhere,” Jessie continued, dropping her amorous demeanour but keeping her focus firmly on Cloud, “and it doesn't matter because all anyone else ever sees is just another character.”</p><p>Cloud's mind began racing with thoughts of how this evening could progress now that his suspicions were finally confirmed, something which made him even more nervous than before. The gorgeous woman he'd come to know and appreciate in such a short time was offering him something he desperately wanted but didn't know how to accept.</p><p>“And when people call you on it?” he asked his companion who'd picked up on his hint of doing just that, but who was also taking care to note his attempted subtlety.</p><p>“Oh don't worry,” she replied, unsure as to whether he got its double meaning, “there's always enough artistic license in there to mix it up. Even Biggs, and Wedge know what I'm like with no idea about the real me.”</p><p>Hearing Jessie talk about her friends so casually brought Cloud back from the moment he now found himself in, and made him think about his own. He felt Jessie's gaze piercing through him as she waited for him to reply, and he had to look away. His eyes found the wall although they were looking at who was sleeping soundly on the other side. He couldn't help but feel guilty at the way he'd even thought about getting this close with one of her friends so soon after finding her again.</p><p>“I completely understand if you don't want to.” Jessie said quietly, berating herself for being so impulsive. “But Tifa always said how she got over you when you never went back home, and so I...” although it wasn't until it was too late that she realised what she'd said as Cloud's eyes returned to her once more, she chided herself again for inserting herself too deeply between childhood friends who still hadn't fully caught up after so long apart.</p><p>“Look, I'm just here because I wanted to have some fun and let off some steam.” All pretence and even her intensity was dropped as Jessie belatedly continued her being straight with Cloud. “I figured there was no harm in asking, but getting between you and Tifa is the last thing I'd want to do. I'm sorry.”</p><p>“It's ok, I get it.” Cloud reassured her. He imagined Tifa being on this side of the wall and standing where Jessie was now, and wondered how she'd be feeling. What it was that she'd offer, and what she'd want in return. “To be honest, I don't think think I could give anyone anything more than just letting off some steam right now anyway.” Jessie gave him a reluctant smile, one that understood where he was coming from. “So you and Tifa talk a lot then, huh?” Cloud asked.</p><p>“We may not go back as far as you two, but we've grown close and gotten to know each other pretty well.” Jessie explained with an expression that apologised for already having given away one too many of the secrets that had been entrusted to her. Cloud looked into her eyes and could finally see the real Jessie that would never do anything if it meant betraying their mutual friend, and how she wanted nothing more than tonight just being tonight.</p><p>In return she looked back into his own eyes as they reflected the look of sympathetic longing, and the only thing that she could see even more than how much he wanted this, was that his reluctance was more than just whether he should, it was whether he could.</p><p>“How about this,” Jessie asked, as she brought her hands to the clasps that kept her sturdy protection in place, “I'll take off my armour, if you take off yours?” She freed her arms from its shoulder pads and lifted its bulk over her head before placing it on the floor behind her. Although she realised that she was instinctively bending over in a way which was most likely teasing Cloud, she also figured that if they were going to do this then they might as well embrace it. Still bent over she continued to take off her heavy boots, her posterior still facing the impassive mercenary that she could feel her passion stirring for.</p><p>As she turned round slowly she caught Cloud gazing at her rear. Combat khakis weren't exactly the sexiest of bedroom attire, so she figured he must really be interested. The thought that she wasn't here in vain made her want him all the more, but his swift look away when she caught him meant that his hesitation was still so obvious. She took a step closer and brought a hand to his cheek as she looked him in the eye.</p><p>“You know I'm more than willing for the rest to come off. But now it's up to you. Let's see if it doesn't soften a few of those hardened edges of yours shall we?” She glanced down as she finished speaking, and saw what she was expecting at the sight of the bulge in his trousers.</p><p>“Glad you're still hardened in all the right places though” she smirked, as she stepped back, allowing him to take in her full body once more. Cloud looked down too, if only to see how obvious his body's reaction was, and realised it really was unmistakable. With nothing left to lose, he took a step towards with her, and reached out to lift Jessie's chain mail over her head.</p><p>“That's more like it!” she exclaimed with her biggest grin of the evening so far, and when his hands were above her head, she placed her lips against his. As soon as her arms were free she wrapped them around his waist, and used the leverage against his body to strengthen her lips resolve as she brought her tongue into the mix. Once Cloud had returned the gesture, she lessened her grip and began to remove her gloves.</p><p>Cloud falteringly reproduced the movements her tongue was making, as Jessie revelled in the clash between his enthusiasm and hesitance. Until now Jessie had presumed that being a first class member of SOLDIER would have meant Cloud having his pick of women, even if it was just for the physical thrill, but the way he kissed her back made her think otherwise. The way he'd placed his hands on her hips showed he was eager, but Jessie switched things up with her kiss, and began to take her time with her tongue.</p><p>She made her movements more distinct, more obvious, and was pleased that this made it easier for Cloud to get into the right rhythms. A few subtle moans also helped him along, and it wasn't long before they had both picked up the pace again, and when she had removed his gloves Cloud's confidence had extended back to removing her own clothes once more.</p><p>“Don't worry, this one's a little tricky” she said, as it was only after he found her body suit's zip that he realised it was a full leotard. “How about you get my belt instead?”</p><p>Cloud undid the buckle of her belt, and loosened it around her waist, but it wasn't until Jessie gave her hips a little shimmy that he realised exactly how loose they had become. Jessie made sure her trousers slid down her legs with ease, and stepping out of them with a hop, she kicked them deftly behind her. A move which, whether alone or with company, had been practised a thousand times over.</p><p>With her hips and legs having captured his attention, it wasn't until Cloud looked back at her in surprise admiration that he realised she had already begun to pull her body suit down, and was beginning to reveal her cleavage. She held it in the perfect position to show off enough of the tops of her bosom; just the right amount to tease Cloud before he made the final decision.</p><p>“This is it, point of no return” she affirmed, “your call.”</p><p>Slowly Cloud took hold of her hands and brought them lower. Jessie followed his lead, but was able to guide his hands to make sure she was manoeuvred out of her top in a way which was both comfortable and triumphant. Jessie paid special attention to notice Cloud's reaction to the bounty of their joint effort of fully uncovering her breasts, and was pleased to see how transfixed he was.</p><p>Cloud marvelled at her bare chest, his eyes taking in the sight of her pert round bust, and watched in fascination as he could see her nipples compose themselves thanks to both the chill of being exposed, and Jessie's desire to unveil even more.</p><p>Cloud's reaction left Jessie herself to completely remove the rest of her garment, and she bent down low, but kept her eyes on Cloud as she did so. Casually exaggerating her movements, making sure her breasts deliberately swayed with the flow of stepping out of her clothing, she made a not so subtle motion towards Cloud's sword as she couldn't resist teasing him further.</p><p>“See, I'm not just overcompensating like other people.” Cloud's face made it obvious that he was more annoyed at hearing the same joke for the hundredth time than taking it personally, but Jessie still felt the need to comfort him, “Relax, I'm just kidding. Here...”</p><p>Jessie grabbed both of Cloud's hands, brought each one to her respective breasts, and then clung to him once more in a passionate kiss before he even had time to respond. It took Cloud a while to rearrange his hands in such a close embrace that she'd brought their bodies into, but eventually managed to free one arm with which he returned her grasp. As their bodies became tighter, and with her skin more exposed, Jessie felt the pressure of Cloud's rigidity against her stomach growing. The hand still at her breast had found something that it obviously considered to be pleasing.</p><p>She could tell Cloud was as eager to please her as he was to please himself, but she also began to change tactics before his fumbling became too much. She pulled his braces over his shoulders and set to work on the buckles around him in a way that reminded him she was now free from hers.</p><p>Allowing Jessie the access she needed, he caught sight of the black knickers which were now the only piece of clothing she still wore. Hardly the practical utilitarian chic conveyed by the rest of her attire, the more intimate part of her underwear was much more provocative than the thicker material around her hips which was always slightly on show. His now unencumbered view showed the true Jessie that remained underneath, in more ways than one; depicted through the lacy patterns that were normally hidden, but which hid very little themselves.</p><p>“Sometimes knowing you look good helps you feel good, you know?” Clouds eyes remained at her crotch as she took a step back to give him a better view. By standing more in the light she also allowed the modest damp strip that had formed in the middle to catch his attention.</p><p>“That means they're ready to come off” Jessie whispered as she moved back closer, and brought his hands to her hips, expertly placing his thumbs at the top of their waist band where they also caught the waist of her silky skin. He pushed his hands in further, and as he leaned in to kiss her once more they curved round to feel the soft cushioning of her buttocks. Jessie placed her hands under Cloud's shirt, and savoured the feel of his muscles as she began to lift it higher, breaking their kiss only for an instant as she brought it up to his face, and considered the parting of their lips was a sacrifice worth making to reveal his muscly torso.</p><p>When their lips found each other again, Cloud found his courage and took this opportunity to bring his hands, and Jessie's knickers, down her thighs. With her undergarments firmly in Cloud hands, and his face moving down her chest and closer than ever to her crotch, Jessie stepped out of them, and performed a twirl as soon as they had been removed from both of her legs.</p><p>“You like?” Jessie asked as she watched Cloud take in the full view of her naked body. She moved her hips to show off her smooth pussy, modelling for him in different positions so he could take it all in. “One of my room mates works at the Honey Bee Inn and brings home some make up and beauty stuff for the rest of us every once in a while. Only I haven't figured out anything past the 'all or nothing' stage yet...”</p><p>“You don't have to explain,” Cloud responded. “I like.”</p><p>His vocabulary might not have expanded much, but even that one small compliment was enough for Jessie to tell that he was finally beginning to properly unwind.<em> And all it took was the sight of my naked body.</em></p><p>“Although I have to say it's rude to stare, Mister”, she jokingly exclaimed, “especially when there's something I could be staring at too.” She paused just long enough to give Cloud a sly wink, and quickly brought her hands back to his trousers which would soon be joining hers on the floor.</p><p>She knelt down in front of Cloud and finding two pieces of material at once, she pulled them both down together to fully expose him. With her face level with his groin, Jessie bit her lip as she revealed his rock hard penis, and revelled at the exhibit finally in front of her. She fantasised about taking it into her mouth there and then, but as Cloud uneasily shuffled his feet free to stand there completely naked, she returned to a standing position in front of him, and took hold of nothing more than his hands.</p><p>“Well it certainly looks like you're enjoying yourself as much as I am,” she began, unable to resist another peek at his cock which stood to attention so close to her own throbbing loins, “but I'm not gonna take anything for granted” she reassured him.</p><p>Cloud watched as Jessie made a show of taking her time to make herself comfortable as she lay herself down on his bed, and noted how much her striking red bandana stood out even more against her completely naked body. She paid particular attention to how much her legs were parted, and brought her arms against the wall and above her head which she rested on his pillow. She made sure her body was mostly neutral, but still open to what she hoped would be Cloud's imminent advances. Her breasts had naturally receded now she was horizontal, though her nipples still stood to attention, as enticing as the single finger she was using to beckon him to join her with. As much as she looked at Cloud in a way that reminded him that where the evening went from here was still his choice, there was also no mistaking how much she herself wanted this to happen.</p>
  </div></div>
<a name="section0002"><h2>2. Chapter 2</h2></a>
<div class="story"><div class="userstuff module">
    
    <p class="western">Unsure where to begin Cloud made his way towards the bed, his body level with Jessie's chest where his dick was within easy reach. With the same hand she had used to summon him, Jessie again reached out and made contact with the weapon to which the merc for hire had granted her sole access.</p><p class="western">“Mmmm, I can hardly wait,” she moaned as she softly wrapped her fingers round his shaft, keeping her eyes on the tip as her delicate strokes elicited a single drip of his growing desire. She watched it trickle down until it reached her fingers and was unsure who she was teasing the most, Cloud or herself. “But let's not get ahead of ourselves, shall we?”</p><p class="western">Having studied him throughout the evening she was slowly figuring out the nuanced reactions of his indomitable features. She began to see more and more of the Cloud that he kept hidden, and the token expressions of his comfort became easier to register. This was hardly an everyday occurrence for him, and Jessie would never forgive herself if she pushed him too fast, nor would she allow the night to be over any quicker than it needed to be. She shuffled over and allowed him to join her, something he did by sitting with one cheek on the edge of the single bed, his face and cock angled towards her.</p><p class="western">“Well hi there stranger”, she playfully acted, her hand settling on his knee “you wanna lay down here with me?” Her hand began to stroke his leg and her fingers delicately made their way to his inner thigh. While she felt him initially tense at this unfamiliar sensation, she saw him easily warm to it once the jolt had abated. It made her smile to see him savour the closeness of someone else's touch somewhere seemingly so innocent, but really so private. Her fingertips began to lightly skim his skin until he cautiously picked up her hand, but only to move it as much as was needed to position to himself next to her completely. She allowed him as much space as she could manage, and as he joined her in the confines of a space intended for one, forgave him for making sure that his most intimate features kept a respectful distance from her own.</p><p class="western">Once he had settled she took her hand, still being held by his, and brought it to her breast, her fingers grazing her nipple. This time she could feel Cloud's pulse quicken at his hand just being so close to her chest, and without her tight embrace to keep it there she chuckled as he withdrew it. Not out of panic, or doubt, but almost out of reverence. As though despite being naked together in their current cramped conditions, despite guiding his hand with hers which still bore his slick mark, he was courteous enough to wait for a formal invitation.</p><p class="western">She wasn't sure if it was the openness of the way things had turned, or even just the way their pace had slowed since they'd done so, but it pleased Jessie to be spending such quality time like this with someone who wasn't only after one thing. The more she got to know him the more she found that Cloud was someone who deserved that bit of extra effort, and she was more than happy to accommodate the deference he was giving her.</p><p class="western">Both on their sides with their faces so close, Cloud's eyes were focused on Jessie's until she raised her leg with obvious intent. His attention was diverted as her limbs parted ways, creating a better angle for his vision, and much more besides, to access what she was offering him. “You don't have to do anything with your hands you don't want to,” she could tell as she spoke that he desperately craved to slip his fingers between her thighs, between her eager wet lips, “but you know by now you can put them anywhere you do want without asking, right?”</p><p class="western">Cloud was hardly the first that she had shared a bed with, even one as snug as this, but for all of his hesitations in touching her where she craved to be touched, more than anything else she only felt relief, and an increasing ability to unwind in his presence. How many men had returned her flirting by feeling up her armour far too vigorously, and not let up when she'd taken it off? How many had expected it all as quick as a wink compared to the man she was with now? Someone who showed appreciation for being with her and not just her body.</p><p class="western">Cloud hardly needed to pull Jessie's face towards his as their tongues convened across very little distance, and he put his arm round her body as she brought herself up against his. He brought his hand down to her backside and took hold of one of her cheeks, his firm grip bringing her body closer, leaving no doubt that she could feel his hard cock, and its brewing excitement, which twitched against her belly.</p><p class="western">She complimented his movements with her own hand holding him closer still, and began to creep her fingers towards the top of his crack, playing with the delicate spot where his lower back became a lot more personal. Rather than following her lead with his own hand as she was expecting however, he instead brought it between them and finally took hold of her breast by himself. Taking her by surprise at first he made her jump, but she soon reassured him it was more than welcome, and he initiated his impassioned massage in earnest.</p><p class="western">Although the fact he was well meaning meant he was a far cry from most, that didn't mean Jessie would simply make do with his inexperience. Usually she'd twist her partners advances to satisfy her own pleasure more than theirs, but with Cloud her proficiency took a different approach. Not that teaching him to use his appreciation more tenderly would be entirely selfless, nor indeed absolutely necessary as she felt his tongue against hers and imagined where else such a new found fervour could be put to good use. It was clear that he was the type to only spend time with those he considered had earned it, but that wasn't any reason they should have to settle for just his good intentions.</p><p class="western">Luckily for Cloud at least, the skills Jessie had acquired had been with men who hid behind their bravado for more selfish reasons, and she knew how to tread delicately lest their fragile egos took offence, and she lose all their attention completely.</p><p class="western">She began to reposition herself, but kept her lips playing with Cloud's as long as she could, only bringing her neck to his mouth when they finally parted. She gasped softly the instant his tongue touched her skin, and used the moment to pause where she was before gradually lowering herself back onto the bed. Cloud obediently followed as he continued to caress her flesh, and his eager hands began to lighten their touch to match his kisses. Jessie reclined as far as she could, and soon began to forget that her current position had begun with just another act. She brought her fingers up to Cloud's spiky hair as his attention began to drift from her moans, and his caressing lips made their way closer to her breasts.</p><p class="western">As Jessie's skin beneath his mouth became softer he moved his hand down to her hips; the fact he'd placed it completely in line with her aching loins was all Jessie could think about until Cloud's tongue found her hard nipple and her attention was redirected again. But as he began to suck on her yielding bosom, his thoughts began to quicken.</p><p class="western">Was he doing things right? How much of a 'right' as opposed to 'wrong' way was there to begin with? He tried to focus more on how Jessie was reacting, but instead found himself worrying about his own reactions and exactly how sticky her leg was becoming because of his own body's uncontrollable exhilaration.</p><p class="western">He lifted himself up and brought his lips to her other breast, coming to this one afresh and letting his instincts decide how to pursue his and his companion's equal pleasure, a more natural fit for them both if Jessie's reactions were to be believed.</p><p class="western">She couldn't help but notice how he'd taken his time from one nipple to the other, not just through the lack of titillation, but she could sense him composing himself, taking a moment to regroup before deciding on his next course of action.</p><p class="western">Jessie could hardly complain about his tactics as her satisfaction was instantly expanded when he reconnected. His movements were slower, his tongue was lighter, and his lips were more controlled. They now nuzzled her nipples each time they enveloped them, and the way they gently tugged back when holding on as long they could tantalised her senses and kept her wanting more. She leaned forward and gently kissed the top of his head. Her lips remained still but the act of being pressed against him was the only way she could return her affection as her body refused anything more than lie there and welcome his advances.</p><p class="western">With his mouth having found its confidence as well as its rhythm, Jessie felt his hand slide from her hip to her groin, and could hardly contain herself as his fingers brushed against the slit between her legs. She had no problem taking her time with Cloud's hesitation, but couldn't deny that doing so had only heightened her desire to feel any part of him inside of her. She brought Cloud's face back to hers, telling herself that kissing him once more would keep her from squealing at his touch. She also willed herself to believe that focusing solely on her pussy would be for Cloud's benefit rather than hers, but ultimately remained unconvinced as her cravings were about to be fulfilled. As she shifted her legs and widened the gap between her thighs, Cloud steadied his hand by placing his palm on the smooth skin above her vulva and began to stroke the eager lips beneath.</p><p class="western">Their surface was slicker than he expected, and his fingers almost found themselves sliding past her velvety crevice completely. Jessie's patience had paid off for them both it seemed, or whether this was typical or a sign that he needn't worry about his performance, Cloud merely composed himself and took his time as he began his second attempt. He brought two fingers back to her unfolding frontier, and could feel Jessie moan against his kiss as they slid effortlessly against her.</p><p class="western">They deftly embraced her as individual strokes encompassed each of her lips, each fold taking it in turns to be surrounded by his digits on all sides before their slippery nature ensured they at last found themselves in the sleek furrow between them all. Jessie's moaning became harder to contain at the touch of his hand as it skirted between her opening and her hooded clit, both crying out to be the centre of attention.</p><p class="western">Cloud began to stroke her in circles. Though her hole was unmistakable, and almost unavoidable, he kept his fingers roving as though he was seeking out something he knew to be there. Jessie's lips enjoyed being spread as he explored his surroundings for something that remained elusive, but it wasn't long before Cloud decided not to lose track of his main intention. Wanting their night to last as long as it could, he would make sure there would always be time later.</p><p class="western">Jessie gingerly arched her back as he finally slid his fingers inside her; her compelling him to reach his potential had finally paid off and he had complete control of her pleasure. Slowly pistoning their way in and out of her moist loins before delving inside once more, it wasn't long before he began to experiment. He began to switch up the amounts of pressure he applied to different places, even curling his fingers into different shapes. It wasn't long until he found that Jessie's appreciation became more amplified with him walking his fingers, one at a time, against the rutted region of her inner walls.</p><p class="western">As she hardly expected much articulation from Cloud, a man of few words even when he wasn't lost in concentration at her pelvis, unlike with others she made an extra effort not to be so vocal in her excitement, but it was a battle she was rapidly losing.</p><p class="western">“Ohhhh, fuck yeah” Jessie exclaimed as she freed herself from Cloud's passionate kiss, needing to catch her breath as much as enunciate her rapture. Once more attempting to contain her enthusiasm again after her sudden outburst, it wasn't long until her flailing arm took hold of Cloud's abiding cock as it searched for something to latch onto. With her other hand gripping the bed, she made sure she wasn't the only one diligently gratifying her partner.</p><p class="western">As she wrapped her fingers around its girth she wondered if it had grown even more since the first time she laid her hand upon it? Or was it merely the fact he was almost as slick as she was, forcing her to grab even harder to keep the friction when sliding her fist up and down his shaft.</p><p class="western">Cloud's lips found her neck once more, and delighted himself in listening to the pleasing moans that Jessie was making as they both played with each other so intimately. With his palm continuing to press her loins towards his fingers still revelling inside of her, Jessie's rapture was building more than ever. Although she was impressed with the physical stamina of his arm which kept him dominating above her for so long, as his breathing became deeper and heavier she wondered if the limits of his excitement would soon over take hers which was rapidly being brought to its peak.</p><p class="western">It was only when Cloud removed his hand from playing with her to stop her playing with him that she realised in the chase for her climax that the speed of her motions had grown considerably faster than her fellow participant, and she'd lost track of his own frenzied elation. She saw him desperately trying to keep himself composed and make sure her greasy hand was no dirtier than it had been before. The look of his nerves returned for the first time since he'd joined her on the bed, as he struggled to find the words.</p><p class="western">“I'm sorry” he said, “I just...”</p><p class="western">“Don't worry, I don't want this to be over either.” She gave him an encouraging smile as she started to sit up, but had to bring her clean hand up to his face to make sure he was no longer looking away in embarrassment. “Plus I'm not that far behind you myself you know. You really are quite the handyman aren't you!” She winked at him as the calming tone of her voice regained its flirty nature once more, and she found the right tone that buoyed him back up.</p><p class="western">While she was careful that her previous efforts to aid his education had been as subtle as she could make them, she took a gamble with the latest. She'd figured him out enough by now to realise that with his inexperience out in the open, she would be better off addressing it in a way that he could acknowledge overcoming it.</p><p class="western">“Seemed like you were looking for something before” she tiptoed, “how about I help you find it while you relax, then you can play with it as much as you like?” She was relieved when she saw the hint of gratitude emerge on his face which had become stoic once more, and took hold of his hand as it made its way to its latest adventure. Her face was beaming with enough excitement for the both of them as she reasoned that “This way, everybody wins!”</p><p class="western">With her fingers surrounding his, she brought the tip of his index finger to the hood of her clit which she slid back to fully reveal its prize underneath.</p><p class="western">“Just remember to play nice and be gentle, Ok?” With his eyes focused on where she'd placed his hand she couldn't see his expression, but the way he began to softly rub her most sensitive revelation, circling it with ease as his fingers danced around in her wet veneer, she could tell his earlier concerns were already forgotten.</p><p class="western">With his eyes transfixed on his latest curiosity, Jessie brought herself back down to the bed and relaxed once more into the elation that Cloud was providing. Though it was slower to build up than before now her apprentice was learning a new skill to master, she was at least better able to appreciate the attention he was focusing solely between her intimate lips. All she could do was graze her fingertips across his sturdy back as she let her body respond to the delight of his touch all by itself.</p><p class="western">Cloud tried to part her lips and expose as much of her delicate clitoris as he could, but found that she was too damp, and his fingers too big to have much effect. Trying to keep things different he changed tactics and used the flat of two fingers to roll over it instead, something which he was pleased to find evoked Jessie's moans once more. He turned round to face her but saw she had closed her eyes as she devoted all of her senses to his touch. The faint tics of her body as she jerked at the feeling of his fingers caused her breasts to quiver, and her still swollen nipples swayed captivatingly along with them.</p><p class="western">Considering his position Cloud realised he'd have to move in order to achieve his latest desire, but also saw how that could work to his, and Jessie's, advantage. He brought his thumb to her clit, his fingers still satisfying her cravings until there was no mistaking their replacement had found its target, and as he nimbly slid his fingers down her lips and inside her once more, he bent his body down so that her nipples were reunited with his tongue.</p><p class="western">Jessie's eyes opened with a start at the new found direction Cloud's attention had taken, and had to bite her lip to stop her bliss from erupting too loudly. With Cloud's face buried between her breasts as he kissed her supple flesh from one nipple to the other, she cast a quick glance at the wall and thought of Tifa behind it.</p><p class="western">Though she could only wonder what Cloud's reaction would be if he knew the full extent of the secrets that Tifa had shared with her, it was knowing how she felt which stopped her feeling guilty about spending this time with Cloud. Whilst she knew that Tifa would have no problem with their current liaison though, if there was any small possibility that things could be rekindled between Cloud and Tifa in the future, then she decided there and then that she owed it to her friend that Cloud's affectionate touch amplified by an emotional attachment is something she would do everything in her power to make sure Tifa experienced.</p><p class="western">As his tongue continued to gratify Jessie's nipples however, he became aware of the similarities between its circular movements, and those of his thumb. With Jessie still moaning her encouragement, his mouth began to take its trail of kisses from between each breast and down her body. He shuffled himself further down the bed as his lips journeyed closer to their destination, and Jessie let out a little giggle as his tongue caressed her belly button, and her body tensed with anticipation as it slowly inched towards her slit.</p><p class="western">She could tell by intuition that it was Cloud's decision to tease her rather than any reluctance on his part that kept his tongue from completing its journey too quickly, and she brought her hands to her breasts to curb the wait for more stimulation. The dampness on her fingers where Cloud's precum hadn't yet dried found her nipple, and she found herself questioning why she'd spent so much energy on previous companions. As she revelled in the pleasure that Cloud was gifting her, she wondered how many other men could bring her even this close without first attempting, and failing, to pleasure her with the one appendage that Cloud had asked her to leave alone, for the time being at least. Though she imagined the feeling of his hard cock inside of her where his fingers were still sweeping, she happily preferred its absence if it meant she could continue to revel in the delights of his tongue which finally made its way to her clit.</p><p class="western">She glanced down and saw Cloud's mouth blissfully make itself at home at her pelvis, and she playfully held her breasts and squeezed her nipples to compliment her playmate's continued ministrations. Eventually their combined efforts began to have their desired effect, and Jessie felt her body begin to tense and involuntarily shiver. With his mouth still indulging her pussy which pressed itself closer against his lips with each shake of her hips, Cloud too felt the change in her reactions and soon his fingers became faster, and his tongue more erratic. Finally being brought to the edge, Jessie struggled to keep her body still as Cloud slashed his tongue across her in all directions until one final impact finished her completely.</p><p class="western">Though he took Jessie's cry of ecstasy as a sign his tongue could take a much needed rest, he continued to walk his fingers inside her, their motions complimenting the waves of pleasure which permeated her body, radiating out from her hips which continued to spasm.</p><p class="western">As the currents began to ebb, her mind began to calm, and her body's convulsions limited themselves to her lungs as she caught her breath, she brought her hand to Cloud's and had to remove his eager fingers herself.</p><p class="western">“Down boy,” she managed between short, sharp gasps. “I'd say you hit the spot”</p><p class="western">Cloud faced her again, but with his eyes more focused on her still heaving chest, she could tell he'd recovered from his own close call, and her climax had only stirred him on again.</p><p class="western">“Look at you, messy pup” she playfully chided as she held his face and wiped the damp streak that his oral massaging had left on his chin. “Why don't you come and lie down here,” she added, “pretty sure you deserve something special after all that!”</p><p class="western">She propped herself up and helped Cloud lay down where her own body had just been. With Jessie's desires at least somewhat sated, he was unsure what to do as he lay there completely exposed. Though his cock was now fidgeting with anticipation once more, he himself was a little more reserved. He watched Jessie's movements carefully as the only time her face faltered from its smirk was when she knowingly raised her eyebrows at him. She repositioned herself to a kneel, and swung one of her knees over his naked body.</p><p class="western">“And this is where things get interesting” she said as she picked up his hands and placed them on her hips. As they held their position she bent forward and took hold of his hard shaft that was directly beneath her. She gave it a few playful strokes before she held it upright and began to lower herself, and prepared to guide it inside of her. Just as she could feel its tip reach her moist and ready lips however, she was surprised to feel Cloud's hands tighten and stop her from taking him in any further.</p><p class="western">Although her level of experience was still less than she liked to portray, it wasn't until now that she truly began to wonder exactly how much Cloud had, or hadn't, experienced himself. He was young after all, and the more she thought about it, the more she realised you don't become a 1st Class SOLDIER without making sacrifices for the training that must be involved.</p><p class="western">“Is this?” For all her way with words, Jessie wasn't quite sure how to express the question she hadn't expected to be needed. “I mean haven't you...” Cloud's hesitation reappeared, and she began to reassure him the only way she could with his cock still in her hand.</p><p class="western">As she rubbed him gently and tilted herself forward so that it was now their faces which were so close to each other, more than disappointment she was instead pleasantly surprised by this turn of events. Looking back, Jessie thought, Cloud wasn't the only partner who's behaviour pointed at their time together being his first, and anyone could have been fooled by the fact he was a quick learner to think otherwise. In retrospect the achievements he'd made seemed even more impressive, though it was the fact that he never felt the need to deny anything which was the true indication of his character.</p><p class="western">“I knew there was someone who cared about intimacy behind those bright blue eyes” she said, as she stared into them once more. Cloud released his sturdy grip from Jessie's thighs, and gave her a small smile of, appreciation? Understanding? Whatever it was, an unspoken comprehension occurred between them as he dropped his fingers which lightly brushed against the skin of her legs.</p><p class="western">No one would call their tryst emotional, but that wasn't to say it meant nothing to them either. Both had great respect for the other after the missions they'd been on together, and their respective need for the most basic of human contact had allowed them to see the same in each other, even beneath their enigmatic exteriors. Just as Jessie remained grateful that he'd given her this much and still refused to take anything more for the physical sake of it, she was also glad that Cloud was honest enough that he couldn't give her the attachment he felt that going all the way needed at the other end of the scale. </p><p class="western">Maybe this is fate? Jessie wondered. Her time with Cloud was proving to be the most enjoyable she'd had in a long time, and if he was destined to be with Tifa afterall, then she had no regrets about being Cloud's teacher if it meant she now had these astonishing memories to keep herself company when she was alone from now on.</p><p class="western">Jessie shuffled back and brought her hand, sticky from Cloud's cock which was as instinctively aroused as ever, to the bed as she lay down against his chest. Without taking it inside her, she straddled his dick and started to pleasure it with the folds of her pussy as she skillfully brought her weight down upon it. She rocked her pelvis back and forth as her lips straddled his length, and their loins enjoyed each others intimate massage. She leant forward so that her clit could also feel the pleasing pressure from her weight grinding against his shaft, and Cloud pulled her neck down so that his lips could embrace hers once more.</p><p class="western">“But just because I can't have your hard cock filling my pussy,” she reasoned as the pressure of her hips gave him a squeeze as hard as her playful tone, “doesn't mean I can't take it somewhere else.” She gave Cloud a sly wink as she began to slowly crawl backwards, kissing his neck and his chest as she made her way down his body. She circled her tongue around his nipples, but then brought her lips the rest of the way in just a few eager skips.</p><p class="western">With his cock exposed once more she couldn't resist the urge for her hand to please her partner yet again, and had already given him several strokes before she held him up and landed her first impatient kiss slowly and deliberately on the tip of his cock. She closed her eyes as she licked her lips and savoured the taste she had been craving since she first set eyes on his rigid phallus. Unable to break the string that now hung between her lips and his crown, she bent herself forward and took him fully into her mouth.</p><p class="western">Cloud let out a pleasant groan as her lips descended over him, and he felt the warm moist cavern that was her mouth engulf him. Her tongue sneaked its way around his shaft, lapping up their combined taste as her mouth itself began to slide up and down. Her fingers remained at the base of his shaft, though she took him in so deep that little room was left for a full fist.</p><p class="western">Wary of his earlier quandary however, Jessie continued to tease him as much as her hunger allowed. Just because this was likely another of his personal firsts of the evening, that was no excuse not to make it even more memorable. First she took her time to build up a steady rhythm of alternating her mouth with her fist, making sure to continually quench his desires while she gave herself time to swallow the evidence of his growing excitement. When she could resist her yearning no longer however, Jessie planted her lips firmly round his greasy shaft as she began to swallow his precum then and there, and the fresh feeling of the suction against his sensitive member brought with it the familiar feeling of pleasure building up inside of him, waiting to be released. Though not quite as frantic as before, his scrambling told Jessie all she needed to know, and with as much as she could take of him inside her, brushed away her loose hair from in front of her face and gave him a sly wink before continuing with a renewed sense of purpose.</p><p class="western">Cloud brought his own hand to her head as she continued, and tried in vain to keep her hair from being dirtied by the dampness of his crotch, to say nothing of what would very quickly make itself known. While he couldn't keep her hair from getting tainted, his attempts did give him an unbridled view of Jessie's lips as they continued to mount him, and he could see as well as feel his whole cock shudder when the climax of his euphoria burst its way into her waiting mouth.</p><p class="western">As Jessie basked in the swells of Cloud's ejaculations and the payoff she'd spent more than just tonight longing for, she had no trouble getting her rhythm to match his own. While each eruption came too quick to swallow one at a time, she could at least make sure that her mouth was never too full, whilst those bursts in between allowed her to savour the taste on her grateful tongue. Though his ecstasy soon receded, she relished the concluding task of finishing up the final drops from his crown that were being reluctantly squeezed from his spent shaft.</p><p class="western">As soon as they both were satisfied, and she could feel her plaything beginning to soften, she made sure she placed it gently against his torso before letting go. She kept it in view as she lay down next to Cloud, rested her head on his shoulder, and held him close with as many limbs as she could.</p><p class="western">Lying there with Jessie in his arms, Cloud wasn't sure if he could express how indebted he was to her for this novel respite from the harsh life they both lead, and the understanding she'd shown him throughout, no matter how brief it was. But as their breathing slowed to their normal pace, and the world around them began to creep slowly back into their consciousness, he couldn't help but feel their time together, and the freedom to be someone more like himself which it afforded him, was coming to an end. They lay there for several minutes, each silently holding the other until Cloud's thoughts regained their overbearing nature and forced him to be the one to speak.</p><p class="western">“Are you staying over or heading back?” he asked. “It's not that I mind, I just don't want things to get complicated. With Barrett and the others.”</p><p class="western">“It's OK if you mean with Tifa,” Jessie replied, “I get it.” Though she was sad that his armour had built itself back up once more, she couldn't fault him for asking. “But you're right, we don't want things to get in the way of the mission.”</p><p class="western">Cloud's reply was a simple silent nod, but he made no move to bring an end to their precedings.</p><p class="western">“Not just yet though, OK?” Jessie asked as she held him tighter. “I don't think I'm the only one who needs this part as much as anything else, am I?”</p><p class="western">Cloud silently lifted her from his frame and began to roll himself away from her. Though she knew that tonight wasn't going to lead anywhere further, Jessie began to curse herself for thinking that once his shielding had returned, Cloud could react any way other than this now that his frustrations and his desires had been satiated. She began to heave herself up to a sitting position when Cloud reached behind him and took her hand and pulled her arm around his waist, slightly tucking his legs up as he did so. As Jessie snuggled in behind him, she interlaced their fingers, and clutched their arms around his chest, their naked skin pressed tightly against each other.</p><p class="western">Without saying a word Jessie gently kissed Cloud on the shoulder and found the abandoned blanket which she draped over them both as they lay there together in the feel of each others warmth.</p>
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